Epoxy Coenzyme A Thioester Pathways for Degradation of Aromatic Compounds

Ismail, Wael; Gescher, Johannes

doi:10.1128/aem.00633-12

Cited by 29 publications

(31 citation statements)

References 88 publications

(115 reference statements)

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“…Accurate and precise quantification of medium‐ and long‐chain acyl‐CoAs has specific utility for the interrogation of a wide variety of inherited and acquired disorders of metabolism including medium‐ and long‐chain acyl‐coenzyme A dehydrogenase deficiencies . This is also necessary for elucidating the critical role of medium‐ and long‐chain acyl‐coenzyme A thioesters in numerous important cellular metabolic pathways . Long‐chain acyl‐CoAs act as feedback regulators in bioenergetics and cellular carbon metabolism as well as regulating cardiac function at the level of ATP channels .…”

Section: Discussionsupporting

confidence: 75%

Stable isotope dilution liquid chromatography/mass spectrometry analysis of cellular and tissue medium- and long-chain acyl-coenzyme A thioesters

Snyder

Basu

Zhou

et al. 2014

Rapid Commun. Mass Spectrom.

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RATIONALE Acyl-Coenzyme A (CoA) thioesters are the principal form of activated carboxylates in cells and tissues. They are employed as acyl carriers that facilitate the transfer of acyl groups to lipids and proteins. Quantification of medium-chain and long-chain acyl-CoAs represents a significant bioanalytical challenge because of their instability. METHODS Stable isotope dilution-liquid chromatography-selected reaction monitoring-mass spectrometry (LC-SRM/MS) provides the most specific and sensitive method for the analysis of CoA species. However, relevant heavy isotope standards are not available and they are challenging to prepare by chemical synthesis. Stable isotope labeling by essential nutrients in cell culture (SILEC) developed originally for the preparation of stable isotope labeled short-chain acyl-CoA thioester standards has now been extended to medium-chain and long-chain acyl-CoAs and used for LC-SRM/MS analyses. RESULTS Customized SILEC standards with > 98 % isotopic purity were prepared using mouse Hepa 1c1c7 cells cultured in pantothenic-free media fortified with [13C315N1]-pantothenic acid and selected fatty acids. A SILEC standard in combination with LC-SRM/MS was employed to quantify cellular concentrations of arachidonoyl-CoA (a representative long-chain acyl-CoA) in two human colon cancer cell lines. A panel of SILEC standards was also employed in combination LC-SRM/MS to quantify medium- and long-chain acyl-CoAs in mouse liver. CONCLUSION This new SILEC-based method in combination with LC-SRM/MS will make it possible to rigorously quantify medium- and long-chain acyl-CoAs in cells and tissues. The method will facilitate studies of medium- and long-chain acyl-CoA dehydrogenase deficiencies as well as studies on the role of medium- and long-chain acyl-CoAs in cellular metabolism.

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Section: Discussionsupporting

confidence: 75%

Stable isotope dilution liquid chromatography/mass spectrometry analysis of cellular and tissue medium- and long-chain acyl-coenzyme A thioesters

Snyder

Basu

Zhou

et al. 2014

Rapid Commun. Mass Spectrom.

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“…Nitroaromatic compounds are released into the environment because they have wide use as dyes, pesticides, plasticizers, explosives, and solvents (Spain & Gibson, 1991). Aromatic compounds are relatively resistant to biomineralization due to enhanced stability caused by the resonance energy of the aromatic ring (Ismail & Gescher, 2012). The Burkholderia sp.…”

Section: Discussionmentioning

confidence: 99%

Enhancing methyl parathion degradation by the immobilization of Burkholderia sp. isolated from agricultural soils

et al. 2017

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Organophosphate pesticides are of great interest for research because they are currently the most commonly used pesticides. In this study, a bacterial strain capable of completely degrading methyl parathion (MP) was isolated from agricultural soils in central Mexico. This strain was designated strain S5‐2 and was identified as Burkholderia cenocepacia. To increase degradation yields, cells were immobilized on three different supports: powdered zeolite and Opuntia sp. and Agave sp. fibers. The results indicated a significant increase in MP hydrolysis and p‐nitrophenol (PNP) degradation with immobilized cells compared to free cell cultures. Furthermore, immobilized cells were capable of withstanding and degrading higher concentrations of PNP compared to cell suspension cultures. The cell viability in the free cell cultures, as well as PNP degradation, was affected at concentrations greater than 25 mg/L. In contrast, cells immobilized on Opuntia sp. and Agave sp. fibers completely degraded PNP at concentrations of 100 mg/L. To verify that MP solution toxicity was decreased by B. cenocepacia strain S5‐2 via pesticide degradation, we measured the acetylcholinesterase activity, both before and after treatment with bacteria. The results demonstrate that the activity of acetylcholinesterase was unaffected after MP degradation by bacteria.

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“…Recently, new pathways for the degradation of aromatic compounds under oxic conditions were unraveled [38], [39]. These pathways operate primarily in facultative anaerobes and use a hydrolytic mechanism to open the ring of the substrates.…”

Section: Discussionmentioning

confidence: 99%

An Oxygenase-Independent Cholesterol Catabolic Pathway Operates under Oxic Conditions

et al. 2013

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Cholesterol is one of the most ubiquitous compounds in nature. The 9,10-seco-pathway for the aerobic degradation of cholesterol was established thirty years ago. This pathway is characterized by the extensive use of oxygen and oxygenases for substrate activation and ring fission. The classical pathway was the only catabolic pathway adopted by all studies on cholesterol-degrading bacteria. Sterolibacterium denitrificans can degrade cholesterol regardless of the presence of oxygen. Here, we aerobically grew the model organism with 13C-labeled cholesterol, and substrate consumption and intermediate production were monitored over time. Based on the detected 13C-labeled intermediates, this study proposes an alternative cholesterol catabolic pathway. This alternative pathway differs from the classical 9,10-seco-pathway in numerous important aspects. First, substrate activation proceeds through anaerobic C-25 hydroxylation and subsequent isomerization to form 26-hydroxycholest-4-en-3-one. Second, after the side chain degradation, the resulting androgen intermediate is activated by adding water to the C-1/C-2 double bond. Third, the cleavage of the core ring structure starts at the A-ring via a hydrolytic mechanism. The 18O-incorporation experiments confirmed that water is the sole oxygen donor in this catabolic pathway.

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Epoxy Coenzyme A Thioester Pathways for Degradation of Aromatic Compounds

Cited by 29 publications

References 88 publications

Stable isotope dilution liquid chromatography/mass spectrometry analysis of cellular and tissue medium- and long-chain acyl-coenzyme A thioesters

Stable isotope dilution liquid chromatography/mass spectrometry analysis of cellular and tissue medium- and long-chain acyl-coenzyme A thioesters

Enhancing methyl parathion degradation by the immobilization of Burkholderia sp. isolated from agricultural soils

An Oxygenase-Independent Cholesterol Catabolic Pathway Operates under Oxic Conditions

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